Photo by Crystal Provencher

Holiday Homes in Loyalist

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Featured Holiday Homes in Loyalist

Large 5 bedroom Great for Families 2 Kitchens House Levels can be Separated

Large 5 bedroom Great for Families 2 Kitchens House Levels can be Separated

Modern 4BR Harbourfront Century Home

9.8 out of 10, Exceptional, (59)
"We had a fabulous time and the accommodations were perfect for what we needed. We were super centrally located for the activities we did and were able to walk to dinner in downtown Picton. The Dans were super responsive and helpful. I would love to stay here again and highly recommend it. "
Modern 4BR Harbourfront Century Home

Private Retreat Home in Picton Bay - Lake Ontario

10.0 out of 10, Exceptional, (2)
"This Lake house was recently renovated and is sitting on the banks of Picton bay. Cool breezes and lots of shade. Our Host was there to greet us. Then cottage was air conditioned and the beds were comfortable. The four of us had a very enjoyable week at this cottage/home. Lots of chairs were available as well as many outdoor games to entertain children. A+++"
Private Retreat Home in Picton Bay - Lake Ontario

Peaceful waterfront cottage in Prince Edward County

9.6 out of 10, Exceptional, (12)
"The property managers were fabulous and the place was exactly as advertised. We had a great stay."
Peaceful waterfront cottage in Prince Edward County

A Cozy Country House - Family Sized w/ Game Room and Large Property!

7.0 out of 10, Good, (2)
"The house was large, clean and well equipped kitchen. Plenty of space to sit out side by the fire and relax after our bike ride from Ottawa. We enjoyed the ample fire wood Yvonne was great to deal with and very timely in her responses."
The price is AU$889
includes taxes & fees
12 Dec - 13 Dec
A Cozy Country House - Family Sized w/ Game Room and Large Property!

Five star equipped 4 bd, huge lot, woods/trails close to lake, downtown/Queen's

10.0 out of 10, Exceptional, (6)
"This beautifully renovated home is located in a quiet mature neighbourhood and has everything you need. It has a well-equipped modern kitchen. The huge dining room table easily seats 12 people. The huge yard has plenty of space for kids and backs on to a woods. There are lots of games and puzzles. I wouldn't hesitate to stay there again."
Five star equipped 4 bd, huge lot, woods/trails close to lake, downtown/Queen's

Downtown Picton, 3 bedroom.

9.4 out of 10, Exceptional, (3)
"great for walking close to the town and eating. lots of good shopping"
The price is AU$551
includes taxes & fees
1 Dec - 2 Dec
Downtown Picton, 3 bedroom.

Farmhouse w/ pool, wood fired oven, basketball court and centrally located

10.0 out of 10, Exceptional, (50)
"Five of us met at this VRBO property for a long weekend of wine and cider sampling, shopping, touring and walking. The spacious, clean and comfortable house allowed us to each have our own room and to gather easily in the large, well-equipped kitchen, dining room and TV room for a great visit. We were close to many of the attractions in the County , another benefit of the location. It was a very enjoyable weekend away. With thanks to Monica."
Farmhouse w/ pool, wood fired oven, basketball court and centrally located

Luxury Vacation Rental Home in Prince Edward County Ontario

10.0 out of 10, Exceptional, (177)
"Beautiful house for a family weekend back in the County"
Luxury Vacation Rental Home in Prince Edward County Ontario

The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.

10.0 out of 10, Exceptional, (45)
"The property had everything we needed to enjoy a long weekend in the fall. The kitchen was well appointed, and dining in the sunroom overlooking the lake was lovely. Everything was super clean, and comfortable. The host, Patricia was responsive to our inquiries and the bottle of local wine was a nice surprise. It was a great location as it is close to the wineries and we wouldn't hesitate to stay here again."
The Lazy Acre: Waterfront cottage with unparalleled views of Smith's Bay.

Lake Street Carriage House

10.0 out of 10, Exceptional, (84)
"This is a fantastic accommodation. The house is beautiful, clean, comfortable & has everything you need for a wonderful stay. The location is also great as there are lots of restaurants you can walk to & lots of stores & wineries nearby. The hot tub is a lovely bonus! We certainly hope to return. "
Lake Street Carriage House

Spacious Private 5 beds, 2.5 bath House - 2 minutes to 401 (5 mins to Kingston)

Spacious Private 5 beds, 2.5 bath House - 2 minutes to 401 (5 mins to Kingston)

Sunlit + Tranquil 2 Bedroom Home | Rewild House

10.0 out of 10, Exceptional, (1)
"Such a cute, cozy and clean house! Everything was perfect for our little family!"
Sunlit + Tranquil 2 Bedroom Home | Rewild House

Capitan Burn's House on Wellington

10.0 out of 10, Exceptional, (7)
"Impressive comfort in the combination of historic and renovated space. Very welcoming for our group, and great for entertaining throughout the day. Well appointed with kitchen, games, and media options. Extremely walkable to the downtown restaurants. "
Capitan Burn's House on Wellington

Mileva Retreats - Picton, PEC

10.0 out of 10, Exceptional, (4)
"My family of 6 plus 2 dogs selected this property as we were attending (without the dogs) our nephew/cousin’s wedding at the Cape mansion a short walk away. The property location was not only perfect for the wedding but allow us time to stroll the main street of Picton to explore the various shops and coffee houses. There was one very minor glitch when were first arrived but after contacting the hosts, the issue was corrected very quickly and to our complete satisfaction. Very impressed with the...
The price is AU$328
includes taxes & fees
1 Dec - 2 Dec
Mileva Retreats - Picton, PEC

Beautiful 7BR Country Farmhouse with Yoga Studio

10.0 out of 10, Exceptional, (12)
"Beautiful property and house!"
Beautiful 7BR Country Farmhouse with Yoga Studio

Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds

10.0 out of 10, Exceptional, (11)
"Great home with lots of space and everything we needed. Host provided all the details and was communicative. "
The price is AU$917
includes taxes & fees
11 Dec - 12 Dec
Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds

33 Vines Winery & Vineyard

8.0 out of 10, Very good, (15)
"We celebrated a bachelorette and it was absolutely amazing. The wine is also delicious. We took the meditarrean supper and charcuterie board with our stay, which was the best! This place is a hidden gen. Would definately recommend."
The price is AU$1,275
includes taxes & fees
30 Nov - 1 Dec
33 Vines Winery & Vineyard

The Brook, Prince Edward County - 5 acre country estate with spa-like amenities!

9.4 out of 10, Exceptional, (11)
"Very well stocked with everything needed for a large group, hosts were very accommodating"
The Brook, Prince Edward County - 5 acre country estate with spa-like amenities!

Adorable Entire Place with Indoor fireplace

8.8 out of 10, Excellent, (12)
"Convenient location, nice neighborhood, exactly as described, and communication with host was prompt. Overall we're pleased with our stay!"
Adorable Entire Place with Indoor fireplace
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Loyalist

All Suites Whitney Manor

4.0 star property
9.8 out of 10, Exceptional, (192)
"Our suite is lovely, spacious and comfortable. Love the decoration and the configuration of each room. Enjoyed our stay."
The price is AU$302
includes taxes & fees
3 Dec - 4 Dec
All Suites Whitney Manor

Cribs On The Hill

4.0 star property
9.2 out of 10, Wonderful, (218)
"The check in was a bit bumpy (not their fault) but they did a great job taking care of it. The place had everything we needed and some nice extra touches."
The price is AU$232
includes taxes & fees
11 Dec - 12 Dec
Cribs On The Hill

Four Season Waterfront Cottage with firepit/private boat launch

9.4 out of 10, Exceptional, (16)
"Quiet, clean and beautiful. Worth the stay!"
Four Season Waterfront Cottage with firepit/private boat launch
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.